A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole

Autores
Fortes, Margiani P.; Bassaco, Mariana M.; Kaufman, Teodoro Saul; Silveira, Claudio C.
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato-1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied.
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Materia
Eco-.Friendly Synthesis
5-Sulfenyltetrazoles
Cerium Catalyst
Peg-400 as Solvent
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/6074
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/6074
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazoleFortes, Margiani P.Bassaco, Mariana M.Kaufman, Teodoro SaulSilveira, Claudio C.Eco-.Friendly Synthesis5-SulfenyltetrazolesCerium CatalystPeg-400 as Solventhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato-1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied.Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; BrasilFil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; ArgentinaFil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; BrasilRoyal Society of Chemistry2014-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/6074Fortes, Margiani P.; Bassaco, Mariana M.; Kaufman, Teodoro Saul; Silveira, Claudio C.; A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole; Royal Society of Chemistry; RSC Advances; 4; 65; 8-2014; 34519-345302046-2069enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2014/ra/c4ra05625finfo:eu-repo/semantics/altIdentifier/doi/10.1039/C4RA05625Finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:21:08Zoai:ri.conicet.gov.ar:11336/6074instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:21:09.114CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
title A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
spellingShingle A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
Fortes, Margiani P.
Eco-.Friendly Synthesis
5-Sulfenyltetrazoles
Cerium Catalyst
Peg-400 as Solvent
title_short A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
title_full A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
title_fullStr A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
title_full_unstemmed A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
title_sort A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole
dc.creator.none.fl_str_mv Fortes, Margiani P.
Bassaco, Mariana M.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author Fortes, Margiani P.
author_facet Fortes, Margiani P.
Bassaco, Mariana M.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author_role author
author2 Bassaco, Mariana M.
Kaufman, Teodoro Saul
Silveira, Claudio C.
author2_role author
author
author
dc.subject.none.fl_str_mv Eco-.Friendly Synthesis
5-Sulfenyltetrazoles
Cerium Catalyst
Peg-400 as Solvent
topic Eco-.Friendly Synthesis
5-Sulfenyltetrazoles
Cerium Catalyst
Peg-400 as Solvent
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato-1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied.
Fil: Fortes, Margiani P.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Bassaco, Mariana M.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Rosario. Instituto de Química Rosario; Argentina
Fil: Silveira, Claudio C.. Universidade Federal de Santa Maria. Departamento de Química; Brasil
description The use of CeCl3·7H2O in polyethyleneglycol 400 (PEG-400), as an efficient and eco-friendly promoter system for the convenient synthesis of 5-sulfenyl tetrazoles derived from indoles and pyrroles, is reported. The synthesis entails the [3 + 2] cycloaddition reaction of NaN3 with 3-thiocyanato indoles (including 3,3′-di-thiocyanato-1H,1H′,2,2′-biindoles) and 2-thiocyanato pyrroles. The thiocyanates were conveniently obtained by the oxone-mediated thiocyanation of differently substituted starting indoles, 1H,1H′,2,2′-biindoles and N-aryl pyrroles with NH4SCN. The scope and limitations of the transformation were also studied.
publishDate 2014
dc.date.none.fl_str_mv 2014-08
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/6074
Fortes, Margiani P.; Bassaco, Mariana M.; Kaufman, Teodoro Saul; Silveira, Claudio C.; A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole; Royal Society of Chemistry; RSC Advances; 4; 65; 8-2014; 34519-34530
2046-2069
url http://hdl.handle.net/11336/6074
identifier_str_mv Fortes, Margiani P.; Bassaco, Mariana M.; Kaufman, Teodoro Saul; Silveira, Claudio C.; A convenient eco-friendly system for the synthesis of 5-sulfenyl tetrazole; Royal Society of Chemistry; RSC Advances; 4; 65; 8-2014; 34519-34530
2046-2069
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/content/articlelanding/2014/ra/c4ra05625f
info:eu-repo/semantics/altIdentifier/doi/10.1039/C4RA05625F
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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